Sodium Carbonate → HCID 57584963, compound

HRID 2077523Notes

Reaction equation

Br[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][NH:6]2.CC1(C)C(C)(C)OB([C:19]2[CH:31]=[CH:30][C:22]3[N:23]=[C:24]([NH:26][C:27](=[O:29])[CH3:28])[S:25][C:21]=3[CH:20]=2)O1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH:6]1[C:7]2[C:3](=[C:2]([C:19]3[CH:31]=[CH:30][C:22]4[N:23]=[C:24]([NH:26][C:27](=[O:29])[CH3:28])[S:25][C:21]=4[CH:20]=3)[CH:10]=[CH:9][CH:8]=2)[CH:4]=[N:5]1

Participants

Conditions

Temperature: 95 °C

Procedure

4-Bromo-1H-indazole (96.8 mg, 0.491 mmol), N-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazol-2-yl)acetamide (193.2 mg, 6.072 mmol), and tetrakis(triphenylphosphine)palladium(0) (51.5 mg, 44.6 μmol) were suspended in 1,4-dioxane (2.0 mL) and sodium carbonate (0.50 mL, 2M in water, 1.0 mmol) was added. The flask was fit with a reflux condensor and placed in a preheated oil bath (95° C.) and stirred under nitrogen overnight. The mixture was then cooled to RT and filtered through a pad of Celite® (diatomaceous earth). The filtrate was concentrated and purified on HPLC (10-95% MeCN/water with 0.1% TFA over 40 minutes) to give N-(6-(1H-indazol-4-yl)benzo[d]thiazol-2-yl)acetamide. MS (ESI pos. ion) m/z: 309 (MH+). Calculated exact mass for C16H12N4OS: 308.

Workup

customplaced in a preheated oil bath
temperatureThe mixture was then cooled to RT
filtrationfiltered through a pad of Celite® (diatomaceous earth)
concentrationThe filtrate was concentrated
custompurified on HPLC (10-95% MeCN/water with 0.1% TFA over 40 minutes)

Sources & evidence

ORD record: ord-88b531924e174eaba634930a76313e25
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07928140B2

Reaction notes

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